When John Tavares' contract ran out with the New York Islanders, he took the opportunity to talk with other teams.
"I felt like I owed it to myself to see what else was out there," Tavares said.
Tavares' exploration led him to rediscover his childhood affinity for the Maple Leafs, and his confidence in Toronto's future led him to sign a monster $77 million, seven-year contract. The Islanders were left with nothing, a mistake other NHL franchises seem determined not to make.
Don't wait. Sometimes not even a day.
On Sunday, when Tavares' departure left a void on Long Island, the Sharks signed Logan Couture, Coyotes signed Oliver Ekman-Larsson, Kings signed Drew Doughty and Lightning signed Ryan McDonagh to long-term deals. None of them would have been free agents until July 1, 2019, and this was the first possible chance to ink extensions that begin more than a year from now.
It's worth every penny to San Jose, Arizona, Los Angeles and Tampa Bay to get those contracts done now rather than risk a key player even exploring unrestricted free agency like Tavares did.
"If you wait too long and you get into the situation where they have the potential to walk or explore the UFA market, that can be challenging times," Sharks general manager Doug Wilson said.
The Ottawa Senators are trapped in such challenging times. They made a contract offer to Norris Trophy-winning captain and 2019 free agent Erik Karlsson, but it's not a great sign that the real negotiating is only just beginning.
"We're not going there," GM Pierre Dorion said. "We don't really want to talk about roster players, contract negotiations, trades, all these things, but I think we owe it to our fans and we made a promise at the town hall that we would make a contract offer to Erik Karlsson and we've done so."
Tick, tick, tick. Even a year away, the pressure is on the Senators to sign Karlsson long term or trade him before the deadline so they don't end up like the Islanders.
The Coyotes made sure they wouldn't be in that spot by locking up Ekman-Larsson to a $66 million, eight-year deal that the soon-to-be 27-year-old defenseman called "a no-brainer." Arizona GM John Chayka calls it "a huge moment for our entire organization" because there's now no fear of losing Ekman-Larsson for nothing.
"A superstar-caliber player has the option to basically go to any of the 31 teams and felt the loyalty, felt the belief in what we were doing enough to sign on long term," Chayka said, adding that the Coyotes had to convince Ekman-Larsson with actions that they were moving in the right direction.
The Kings convinced Doughty of that so much, he knew all season he was going to re-sign. He's building a new house in the LA area, is getting married this summer and is ready to start a family in a place he wants to stay for essentially the balance of his career.
"I never wanted to leave there, to be honest," Doughty said. "It will be nice not to answer the question, 'Hey are you coming to Toronto? You're coming to the Leafs, right?' No, I'm not coming to the Leafs, everyone."
Doughty signing for $88 million over eight years sets the bar for Karlsson, who could face similar questions if he goes into the season without a future contract like Tavares did. Over the past week, Tavares began wondering if he would play for his hometown Maple Leafs, a bond too deep for the Islanders to overcome.
Couture grew up not far from Toronto, but he never entertained that possibility because he signed a $64 million, eight-year deal with the Sharks. Couture respected Tavares' choice and made his own without much difficulty.
"We have some very good players: Marc-Edouard Vlasic, Brent Burns, Martin Jones, Evander Kane — very, very good players — Joe Pavelski," Couture said, rattling off core players all signed long term. "I want to win. That's my goal as a hockey player. I believe that San Jose has and will continue to have a very, very good chance at winning in the future. That's why my decision was so easy."
It was just as easy for McDonagh, who signed a $47.25 million, seven-year deal with the Lightning, who acquired him at the trade deadline. McDonagh was comfortable with Tampa Bay, which went through an almost-Tavares situation two years ago with captain Steven Stamkos before signing him on the eve of free agency.
Days after signing Stamkos in 2016, the Lightning extended top defenseman Victor Hedman at the first possibly moment like they did with McDonagh. GM Steve Yzerman knows how to work ahead, which is often essential in today's NHL with important players.
"(If you wait), you don't really know how it's going to go," Yzerman said. "We go into next year for both parties, we don't know, and I think it's worthwhile exploring the opportunity now."